Potassium Iodide → 2-{1-[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

HRID 238233ノート

反応式

HRID 238233 の反応式
Br[CH:2]([C:4]1[N:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([N:24]2[CH2:29][CH2:28][N:27]([CH:2]([C:4]3[N:13]=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH3:3])[CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 7129241-(4-Bromobenzene-1-sulfonyl)piperazineHCID 599931212-(1-Bromo-ethyl)-quinazoline

生成物 1

HCID 599933482-{1-[4-(4-Bromo-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

A mixture of 2-(1-Bromo-ethyl)-quinazoline (43 mg, 0.18 mmol) and 1-(4-Bromo-benzenesulfonyl)-piperazine (67 mg, 0.22 mmol), potassium iodide (30 g, 0.18 mmol) and potassium carbonate (37 mg, 0.27 mmol) in acetonitrile (1 mL) was heated at 65° C. for 1 day. The reaction mixture was then concentrated in vacuo. The residue was dissolved in dichloromethane and washed with saturated sodium thiosulphate solution, saturated sodium bicarbonate solution and then with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was dissolved in DMSO and purified by HPLC. 1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 8.06 (m, 3H), 7.80 (t, J=7.9 Hz, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.58 (d, J=8.5 Hz, 2H), 4.86 (q, J=7.0 Hz, 1H), 3.65 (m, 2H), 3.43 (m, 6H), 1.88 (d, J=7.0 Hz, 3H) HPLC ret. time 2.45 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 461.1 (M+1)+.

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium thiosulphate solution, saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product was dissolved in DMSO
  7. custompurified by HPLC
  8. custom1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 8.06 (m, 3H), 7.80 (t, J=7.9 Hz, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.58 (d, J=8.5 Hz, 2H), 4.86 (q, J=7.0 Hz, 1H), 3.65 (m, 2H), 3.43 (m, 6H), 1.88 (d, J=7.0 Hz, 3H) HPLC ret. time 2.45 min, 10-99% CH3CN, 5 min

出典と根拠

ORDレコード
ord-87a4c362569442169dae661859783a5f
出典データセット
uspto-grants-2014_02
特許番号
US08642609B2

反応ノート

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